Diisopropylamine → 4-p-Tolylsulfonyl-4,3,3,-trimethyl-pentanenitrile

HRID 435425

반응식

HRID 435425 반응식
[CH2:1]([Li])CCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.C1(C)C=CC([S:19](C(C)C)(=[O:21])=[O:20])=CC=1.[CH3:26][C:27]([CH3:31])=[CH:28][C:29]#[N:30].P(O)(O)([O-])=O.[Na+].[CH2:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>O1CCCC1>[C:38]1([CH3:1])[CH:43]=[CH:42][C:41]([S:19]([C:10]([CH3:11])([CH3:12])[C:27]([CH3:31])([CH3:26])[CH2:28][C:29]#[N:30])(=[O:21])=[O:20])=[CH:40][CH:39]=1

참가 물질

8

반응물 6

HCID 7912DiisopropylamineHCID 8078CyclohexaneHCID 943013-Methyl-2-butenenitrileHCID 8167921-(Isopropylsulfonyl)-4-methylbenzeneHCID 23672064Monosodium phosphateHCID 178418339Butyllithium

생성물 1

HCID 128330284-p-Tolylsulfonyl-4,3,3,-trimethyl-pentanenitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3.81 ml of a cyclohexane solution of 1.75M of butyllithium were added at -30° to -40° C. to a mixture of 1.05 ml of diisopropylamine and 4 ml of tetrahydrofuran and the mixture was stirred for 10 minutes and was then cooled to -60° to -70° C. Then 1.22 g of p-tolyl isopropylsulfone were added to the mixture which after 15 minutes of contact was poured over 10 minutes under an inert atmosphere into a solution of 0.5 g of dimethylacrylonitrile and 4 ml of tetrahydrofuran at -60° to -70° C. The mixture was stirred for 30 minutes at -60° to -70° C. and was then poured into an aqueous saturated monosodium phosphate solution. The mixture was extracted with benzene and the organic phase was dried and evaporated to dryness. The residue was crystallized from isopropyl ether to obtain 0.740 g of 4-p-tolylsulfonyl-4,3,3,-trimethyl-pentanenitrile melting at 126° C.

후처리

  1. temperaturewas then cooled to -60° to -70° C
  2. stirringThe mixture was stirred for 30 minutes at -60° to -70° C.
  3. extractionThe mixture was extracted with benzene
  4. customthe organic phase was dried
  5. customevaporated to dryness
  6. customThe residue was crystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-65212fa3874a4fbfb05ef8243326a26e
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04401601

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